CA2566734A1 - Siloxane-acrylate interpenetrating networks and methods for producing the same - Google Patents

Siloxane-acrylate interpenetrating networks and methods for producing the same Download PDF

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Publication number
CA2566734A1
CA2566734A1 CA002566734A CA2566734A CA2566734A1 CA 2566734 A1 CA2566734 A1 CA 2566734A1 CA 002566734 A CA002566734 A CA 002566734A CA 2566734 A CA2566734 A CA 2566734A CA 2566734 A1 CA2566734 A1 CA 2566734A1
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CA
Canada
Prior art keywords
group
organic siloxane
polymeric binder
silicon
terminal
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002566734A
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French (fr)
Other versions
CA2566734C (en
Inventor
Timothy P. Bender
Barkev Keoshkerian
John F. Graham
Yvan Gagnon
Cheng-Kuo Hsiao
Nan-Xing Hu
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Xerox Corp
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Xerox Corp
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Publication date
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Publication of CA2566734A1 publication Critical patent/CA2566734A1/en
Application granted granted Critical
Publication of CA2566734C publication Critical patent/CA2566734C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
    • C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
    • C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/068—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
    • C08F290/14—Polymers provided for in subclass C08G
    • C08F290/148—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D143/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Coating compositions based on derivatives of such polymers
    • C09D143/04—Homopolymers or copolymers of monomers containing silicon
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
    • Y10S525/903—Interpenetrating network

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Photoreceptors In Electrophotography (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Silicon Polymers (AREA)

Abstract

Siloxane-containing materials that have been prepared by a sol-gel method and polymeric binder materials form interpenetrating networks. Silicon-containing layers including such interpenetrating networks are provided. Methods for preparing interpenetrating networks and silicon-containing layers including interpenetrating networks are also provided. In addition, photoreceptors and image-forming apparatus including such silicon-containing layers are provided.

Claims (20)

1. An interpenetrating network comprising an organic siloxane-containing material and a polymeric binder material.
2. The interpenetrating network according to claim 1, wherein the organic siloxane-containing material is at least one member of the group consisting of organic siloxane-containing materials having at least one reactive double bond.
3. The interpenetrating network according to claim 2, wherein the organic siloxane-containing material is at least one member of the group consisting of organic siloxane-containing acrylates.
4. The interpenetrating network according to claim 1, wherein the polymeric binder material is at least one member of the group consisting of polymeric binder materials having terminal nitroxide groups.
5. The interpenetrating network according to claim 4, wherein the polymeric binder material is at least one member of the group consisting of polyacrylate materials having terminal TEMPO groups.
6. The interpenetrating network according to claim 1, wherein the organic siloxane-containing material is prepared by sol-gel polymerization.
7. A method of preparing an interpenetrating network, comprising:
sol-gel polymerizing a functionalized organosiloxane material to form an organic siloxane-containing matrix;
reacting the organic siloxane-containing matrix with a polymeric binder material having a terminal reactive group.
8. The method according to claim 7, wherein said reacting comprises reacting the terminal reactive group of the polymeric binder material with a reactive double bond in the organic siloxane-containing matrix.
9. The method according to claim 7, wherein the organic siloxane-containing material is at least one member of the group consisting of organic siloxane-containing materials having at least one reactive double bond.
10. The method according to claim 9, wherein the organic siloxane-containing material is at least one member of the group consisting of organic siloxane-containing acrylates.
11. The method according to claim 7, wherein said terminal reactive group is at least one functional group chosen from the group consisting of nitroxide groups.
12. The method according to claim 11, wherein said terminal reactive group is a TEMPO group.
13. The method according to claim 7, wherein the polymeric binder material is at least one member of the group consisting of polyacrylate materials having terminal TEMPO groups.
14. A silicon-containing layer comprising an interpenetrating network that comprises an organic siloxane-containing material and a polymeric binder material.
15. The silicon-containing layer according to claim 14, wherein the organic siloxane-containing material is at least one member of the group consisting of organic siloxane-containing materials having at least one reactive double bond.
16. The silicon-containing layer according to claim 14, wherein the polymeric binder material is at least one member of the group consisting of polymeric binder materials having a terminal nitroxide group.
17. The silicon-containing layer according to claim 14, wherein the polymeric binder material is at least one member of the group consisting of polyacrylate materials having terminal TEMPO groups.
18. The silicon-containing layer according to claim 14, wherein the organic siloxane-containing material is prepared by sol-gel polymerization.
19. An electrophotographic photoreceptor comprising a silicon-containing layer, wherein the silicon-containing layer comprises an organic siloxane-containing material and a polymeric binder material.
20. The electrophotographic photoreceptor according to claim 19, wherein the silicon-containing layer is an outermost layer.
CA2566734A 2005-11-07 2006-10-31 Siloxane-acrylate interpenetrating networks and methods for producing the same Expired - Fee Related CA2566734C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US11/267,336 2005-11-07
US11/267,336 US7517928B2 (en) 2005-11-07 2005-11-07 Siloxane-acrylate interpenetrating networks and methods for producing the same

Publications (2)

Publication Number Publication Date
CA2566734A1 true CA2566734A1 (en) 2007-05-07
CA2566734C CA2566734C (en) 2011-07-26

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
CA2566734A Expired - Fee Related CA2566734C (en) 2005-11-07 2006-10-31 Siloxane-acrylate interpenetrating networks and methods for producing the same

Country Status (3)

Country Link
US (1) US7517928B2 (en)
JP (1) JP5175045B2 (en)
CA (1) CA2566734C (en)

Cited By (1)

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Publication number Priority date Publication date Assignee Title
CN109666167A (en) * 2017-10-17 2019-04-23 翁秋梅 A kind of hydridization dynamic aggregation compositions

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US7713499B2 (en) * 2006-04-28 2010-05-11 Xerox Corporation Fluidized bed reaction apparatus and methods for using the same
SG11201609628UA (en) 2014-05-20 2016-12-29 Whitford Corp Sol-gel compositions with improved hardness and impact resistance
EP3250618A4 (en) 2015-01-29 2018-07-18 Dow Silicones Corporation Silicone acrylate compositions and methods of preparing the same
CN113842507B (en) * 2021-07-19 2022-04-29 浙江大学 Polyelectrolyte hydrogel coating with super-strong substrate adhesion performance and preparation method thereof

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CN109666167A (en) * 2017-10-17 2019-04-23 翁秋梅 A kind of hydridization dynamic aggregation compositions
CN109666167B (en) * 2017-10-17 2023-07-25 厦门逍扬运动科技有限公司 Hybrid dynamic polymer composition

Also Published As

Publication number Publication date
US20070106023A1 (en) 2007-05-10
JP2007131844A (en) 2007-05-31
CA2566734C (en) 2011-07-26
JP5175045B2 (en) 2013-04-03
US7517928B2 (en) 2009-04-14

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